“Dollars to doughnuts”

“Dollars to doughnuts” (or “I’ll bet dollars to doughnuts”) means a sure thing, a certainty; someone will put up something to substance to something worth much less that a certain event has occurred or will occur. The phrase “dollars to dimes” is recorded in horseracing lingo since at least 1844; “dollars to doughnuts” is cited in print from at least 1871.
 
There are many other forgotten variants, including “dollars to buttons” and “dollars to cobwebs.” “Dollars to doughnuts” seems to have been the most memorable formation and is still in use today.
 
 
Dictionary of American Regional English
dollars to doughnuts n Also dollars to a doughnut, ~to buttons, ~to cobwebs
A virtual certainty, something assured; something valuable wagered against something insignificant in a “safe” bet.
1884 (1890) Peck Peck’s Boss Book 130 seWI, It is dollars to buttons that..she will be blown through the roof.
1890 Texas Siftings 8 Nov. 6/3 (OEDS), It is dollars to a doughnut..That some one will start a fire.
1904 Boston Herald 8 Aug. 6 (OEDS), It is dollars to cobwebs thgat every such person will be disappointed.
1904 Utica Observer (NY) 29 June 6/6 NYC, They talk of fire drills;..it is dollars to doughnuts that not an excursion boat in New York harbor ever had one.
1932 Atlantic Mth. 149.390/2, It is dollars to doughnuts not a soul will see him.
1959 VT Hist. new ser. 27.133, Dollars to doughnuts...Usually with bet.  Common.
1968 DARE (Qu. JJ20, If you felt very sure about something, and wanted to show it: “I’m so sure, I’d——it.” Infs. NY93, W134, Bet (you) dolalrs to doughnuts.
 
(Historical Dictionary of American Slang)
dollars to doughnuts [fr. the expression bet dollars to doughnuts [that]; see 1929 quot.] most certain, most assuredly.
1893 Chi. Daily Tribune (Sept. 1) 7: The best he could do was to make a dead heat of it after it had looked dollars to doughnuts that he would be beaten.
1895 Harper’s (Nov.) 856: Dollars to doughnuts Uncle Sam never sees a cent of that money again.
[1901 Ade Modern Fables 33: It was Dollars to Dumplings that many a Moon would Wax and Wane ere George went against that Combination once more.]
1910 T.A. Dorgan, in N.Y. Eve Jour. (Jan. 16) 12:It’s dollars to doughnuts that if ever Steve’s wallop lands first they’ll be picking Mr. THomas up in a dustpan piece by piece.
1929 “E. Queen” Roman Hat ch. x 113: I’ll bet dollars to doughnuts Field played the stock market or the horses.
1945 Dos Passos Tour 224: Dollars to doughnuts I shan’t get to go.
1948 J.H. Burns Lucifer 196: DOllars to doughnuts they’re happy to be getting back.
1966 Shepard Doom Pussy 55: I bet a dollar to a doughnut we can make some wicked music together.
1977 A. Patrick Beyond Law 4: When Tony Baretta couldn’t concentrate, you could bet dollars to doughnuts that it involved his work.
1979 in J.L. Gwaltney Drylongso 210: I’ll bet you dollars to doughnuts they out-know me.
 
(Oxford English Dictionary)
Colloq. phrases (orig. and chiefly U.S.): (it is) dollars to doughnuts (or buttons, etc.), (it is) almost assured; a certainty.
1884 G. W. PECK Peck’s Boss Book 130 It is dollars to buttons that..she will be blown through the roof.
1890 Texas Siftings 8 Nov. 6/3 It is dollars to a doughnut..That some one will start a fire.
1904 Boston Herald 8 Aug. 6 It is dollars to cobwebs that every such person will be disappointed.
1904 Utica (N.Y.) Observer 29 June 6 They talk of fire drills;..it is dollars to doughnuts that not an excursion boat in New York harbor ever had one.
1932 Atlantic Monthly Mar. 390/2 It is dollars to doughnuts not a soul will see him.
1936 J. CURTIS Gilt Kid xiii. 131 If he were seen it was dollars to doughnuts that he would be arrested.
   
29 December 1844, New Orleans (LA) Times Picayune, pg. 2:
After the third heat, it was almost dollars to dimes that he carried off the money, but he had to work for it, the fourth heat being most admirably contested, although the rate of speed abated, as the record shows. 
 
5 October 1856, New York (NY) Herald, “The Turf,” pg. 5:
Fourth Heat.—Dollars to dimes on the mare.
   
11 June 1860, Milwaukee (WI) Daily Sentinel, “The Greatest Trot Ever Made” (From the New York Tribune), pg. 1, col. 4:
The half mile had been done in one minute and ten seconds and now the race seemed Patchen’s—it was dollars to dimes.
       
11 March 1871, Leavenworth (KS) Daily Commercial, pg. 4, col. 2:
It is a dollar to a doughnut that her carroty hair stands out like quills on a fretful porcupine, except when she soaps it.
 
18 October 1871, Portland (ME) Daily Press, “Miscellaneous Notices,” pg. 3, col. 3:
We bet Dollars to Doughnuts that we are offering goods at lower prices than any house in Portland.
(...)
J. H. FITZGERALD’S.
 
Chronicling America
12 June 1873, New York (NY) Herald, “Aquatic,” pg. 4, col. 5:
THE RACE.
Around the new settlement on the Harlem; there was much anxiety regarding the contest; but the majority, in fact, nine-tenths, of the oarsmen thought it was “dollars to doughnuts” that Losee would beat his opponent.
 
California Digital Newspaper Collection
27 October 1875, Sacramento (CA) Daily Record-Union, “Nevada Items,” pg. 1, col. 7:
P. K. Mason, the chap who was arrested at Eureka the other day for stealing a watch and chain from the Antelope lodging house, has been bound over in the sum of $200 to answer before the Grand Jury upon a charge of grand larceny. The evidence against him was conclusive, in regard to taking the watch, but the Sentinel thinks if he states to the jury that he needed it to take medicine by, it’s dollars to doughnuts he will be acquitted.
 
6 February 1876, Daily Nevada State Journal (Reno, NV), pg. 1, col. 6:
...it’s dollars to doughnuts that such person is either mad at the editor because he declined to toady to him, or is owing the office for subscription or advertising. (...)—Eureka Sentinel.   
 
11 March 1876, Daily Nevada State Journal (Reno. NV), pg. 3, col. 4:
HALF FARE.—Several Benoites took a vantage of the half fare tickets offered to those who were to attend the ball given by the railroad boys at Carson last night, and attended it. It’s dollars to doughnuts all enjoyed themselves.
 
3 July 1879, Wall Street Daily News, pg. 2:
The Times-Review says: “It’s dollars to doughnuts that the directors of the Independence declare a dividend in July.”
 
20 March 1885, Kansas City (MO) Star, pg. 3:
Marmaduke has the reputation here of being a man of unflinching nerve, and those who read the letter over Maj. Rainwater’s signature were willing to bet dollars to dimes that the cost of it would be his life, even though Marmaduke holds the position of governor.